Imidazole derivatives modulating the sodium channels

Abstract

A compound of the formula wherein the substituents are defined as in the specification.

1 - 10 . (canceled)  
     
     
         11 . A compound of the formula  
       
         
           
           
               
               
           
         
       
       in which  
       R 1  is alkyl of 3 to 16 carbon atoms or cycloalkylalkyl, the cycloalkyl of which has 3 to 7 carbon atoms and the alkyl of which has 1 to 6 carbon atoms,  
       or R 1  is aralkyl optionally substituted 1 to 3 times on the aryl by at least one member selected from the group consisting of halogen, alkyl or alkoxy of 1 to 6 carbon atoms;  
       R 2  is phenyl optionally substituted 1 to 3 times by at least one member selected from the group consisting of halogen and alkyl or alkoxy of 1 to 6 carbon atoms,  
       or R 2  is biphenyl optionally substituted from 1 to 4 times by at least one member selected from the group consisting of halogen and alkyl or alkoxy of 1 to 6 carbon atoms;  
       R 3  is hydrogen or alkyl of 1 to 6 carbon atoms;  
       it being understood however that: 
 when R 2  is phenyl optionally substituted from 1 to 3 times by at least one member selected from the group consisting of halogen and alkyl or alkoxy, then R 1  is neither alkyl of 1 to 6 carbon atoms nor  
                     
 in which R 9  is at least one to three substituents selected from the group consisting of hydrogen, halogen and alkyl or alkoxy of 1 to 6 carbon atoms, and R 10  and R 11  being hydrogen alkyl of 1 to 6 carbon atoms;  
 when R 2  is non-substituted biphenyl or when R 2  is phenyl optionally substituted from 1 to 3 times by halogen or alkyl or alkoxy of 1 to 4 carbon atoms, then R 1  is neither —(CH2)n-Z in which n is an integer from 0 to 3 and Z is alkyl of 1 to 4 carbon atoms or phenyl optionally substituted by 1 to 3 halogen or alkyl or alkoxy of 1 to 4 carbon atoms;  
 or a pharmaceutical salt thereof.  
 
     
     
         12 . A compound of  claim 11 , selected from the group consisting of: 
 2-(1-pentylhexyl)-4-phenyl-1H-imidazole;    4-(4-fluorophenyl)-2-(1-pentylhexyl)-1H-imidazole;    2-(cyclohexylmethyl)-4-(4-fluorophenyl)-1H-imidazole;    4-(1,1′-biphenyl-4-yl)-2-(1-pentylhexyl)-1H-imidazole;    4-(4-tert-butylphenyl)-2-(1-propylbutyl)-1H-imidazole;    4-(4-fluorophenyl)-2-(1-propylbutyl)-1H-imidazole;    4-(4′-bromo-1,1′-biphenyl-4-yl)-2-(1-propylbutyl)-1H-imidazole;    4-(1,1′-biphenyl-4-yl)-2-(2-cyclohexylethyl)-1H-imidazole;    4-(1,1′-biphenyl-4-yl)-2-[1-(4-isobutylphenyl)ethyl]-1H-imidazole;    4-(1,1′-biphenyl-4-yl)-2-(1-phenylethyl)-1H-imidazole;    4-(1,1′-biphenyl-4-yl)-2-(1-propylbutyl)-1H-imidazole;    4-(1,1′-biphenyl-4-yl)-2-(cyclohexylmethyl)-1H-imidazole;    4-(1,1′-biphenyl-4-yl)-2-(3-cyclohexylpropyl)-1H-imidazole;    and a salt of thereof.    
     
     
         13 . A compound selected from the group consisting of: 
 4-(1,1′-biphenyl-4-yl)-2-(4-isobutylbenzyl)-1H-imidazole;    2-hexyl-4-(4-isobutylphenyl)-1H-imidazole;    4-phenyl-2-(3-phenylpropyl)-1H-imidazole;    4-(1,1′-biphenyl-4-yl)-2-hexyl-1H-imidazole;    4-(4-fluorophenyl)-2-[1-(4-isobutylphenyl)ethyl]-1H-imidazole;    and a pharmaceutical salt thereof.